Should I ask this person out?

[Kevin II]

Hi ladies (or guys too),

I would like your opinions please.

I am really considering asking out the person that cuts my hair. We have really good chemistry and never run out of things to talk about and are always laughing and sometimes having deep conversations as well.

We’ve texted back-and-forth before outside of the salon, sharing playlists and making jokes here and there, not too often but it’s happened a few times.

I guess I’ve known her now for about eight months. She was married and now she is separated, even though mentally, I think she’s been separated for a while and has wanted to get out.

I’ve also talked to her about a pretty brutal break up that I went through with my fiancé last year where I was cheated on a bunch.

So yesterday, we really got deep and I told her about some of the tragedies that have happened in my life, and she did too.

It was kind of funny because she left me under the heat lamp like three times longer than she should have because she was quite enamored with my story.

What usually takes 30 minutes took like an hour, but we really connected on a deep level and I could tell she was really into it. I know she really likes me a lot just as a friend I guess, or a customer, but I would say we’re friends for sure.

Like most men, I am awful at picking up on hints, or misconstruing normal friendly behavior as possible flirting.

When I was sitting in the chair, she kind of put her hands on my shoulders when she was just telling me “oh I forgot to tell you about something” but she kind of put both hands on my shoulders for a little bit and it had nothing to do with haircut. I know that much. 

Does that mean anything? I mean I know it would mean that she feels comfortable around me but, who knows if it means more.

I just found out yesterday that she was separated. I have no idea if she’s seeing anybody but I don’t think she is. I’m pretty positive that she isn’t.

But yesterday, we definitely went deeper than we ever had, sharing some pretty intense personal stuff with each other and we were totally dialed in. We also talked about relationships and what we like and don’t like within the context of them.

Our conversations have always flowed like fine wine and our senses of humor certainly match.

One important note: I am 47 years old and she just turned 30. and I have three kids and she has no kids. I have a feeling that wouldn’t bother her though. She already knows.

I’ve been told I look like I’m probably late 30s early 40s, I guess because I don’t drink and act pretty youthful.

However, my late fiancé was the same age as she is. She was also incredibly gorgeous just like this person. so she knows I’ve had a years-long relationship, which was really successful until the end, with somebody her age.

When I shaved my beard a couple months ago she told me it looked really good, enthusiastically, so I guess she thinks I’m attractive? I don’t know. I think she does. I didn’t ask….she was genuinely surprised when I walked in.

So on the way out yesterday, I wanted to kind of move it along just a little bit but without giving away how I was feeling.

Since she was going through a tough time, I said “look, if you ever need to vent, or just wanna talk to somebody, you can reach out to me anytime and I’ll be there to talk to you.”

She said “thanks I really appreciate you and I really enjoy working with you.”

I don’t know, I kept focusing on the “I appreciate YOU” as opposed to “I appreciate IT,” maybe that doesn’t mean anything?

Then today, I had to text her about a future appointment, and she knew it was coming. But I made a couple of jokes and she laughed and I sent her a couple of playlists, which again I’ve done before, and told her that if she’s ever feeling down, or up for that matter, that she can listen to these. It was music that we had talked about and both like.

She gave both of them the love heart reaction, and another “I appreciate you” with exclamation points.

So we like the same music and have talked about concerts a lot. I thought about perhaps asking her to go to a concert with me, there are three around town that we could choose from that I think she would really like.

I don’t really want to present it as like a real date (or should I?), because that comes with expectations, and I certainly don’t wanna sit across from each other at some fancy dinner.

I’m thinking maybe we go and have a great time and then I could follow up and ask her out officially? Or do I let my intentions be known right away, but perhaps not directly to where she feels pressure? I want her to be totally relaxed. 

I thought about doing something with more than just the two of us, like with her friends, but I really wanna avoid the friend zone up front. 

It’s certainly a delicate balancing act.

How do you think I should handle this? Or should I even pursue this at all? 

It does feel different. It feels like, to me anyway, that I could really be something special.

I know confidence is key but I want to be very careful. 

Also, I’ll need to prepare and get advice about what to do if she says no. I think I would kind of act like it was no big deal and be friendly and continue on with the friendship, and maybe it would turn into something later? I’m not sure.

Any opinions are greatly appreciated!

Thanks 

[mylolita]

Kevin!

You can speculate until the cows come home, but the only way you will ever find out, is to be straight up, shoot your shot, and ask her out!

Call her up! Or, turn up at the salon, maybe even bolder, and even better. Just say, "I wanted to come in and ask you if you wanted to go have dinner with me this week?" She can only say no, she can only say yes. 

If she says, "Is it a date?" Say "Of course." 

There is nothing to fear. She sounds very interested anyway, by the way. This is definitely not the normal hair stylist and customer relationship!!!

Best of luck, but I don't think you're gonna need it!

x

[mylolita]

PS - if she says no, just say, half jokingly, you've broke my heart, but you do a good cut, so I'll let you off 😉

x

[boltnrun]

You have two people who are fresh out of romantic involvements. In her case she's still married.

You described your ex as the love of your life just today on your other thread. So it seems you still have that emotional attachment.

And do you know if this cosmetologist is separated because SHE wanted to be or did her husband initiate the separation? Is she still living with him? 

Are you always attracted to women who are nearly two decades younger? If so, why is that? I'm not saying it's wrong but it is unusual.

I would suggest asking her to have coffee so you can get a gauge on where the both of you are at.

[Kwothe28]

Hairdressers are always talkative with customers. It kinda goes with the job because its in their interest for you to feel good so you would come back. Same with bartenders or any other profession where they depend on you coming back to spend your money there. So I wouldnt read as much as you into situation. She is like that with probably a lot of people.

But, if you want to ask her out, I am always supportive on that. As its way better to know if she is into you or just professional. Just say that you want to take her out for coffee or drinks and see what she says. Its better to know where you stand then to spend months thinking something would happen and that she just doesnt want anything. You can at least take her off the list of potentials and move on. And who knows, maybe she does like you.

Also, be warned: If she says "No", or you start something and it doesnt go anywhere and you broke up, you would be making your trip to hair salon more ankward and would probably need to change it. So, be warned about that if you want to try something.

[Kevin II]

50 minutes ago, mylolita said:

She sounds very interested anyway, by the way. This is definitely not the normal hair stylist and customer relationship!!!

 

I kind of think so too but every time I think that I end up being wrong, well….except once.

I put everything down exactly as is, and yeah I know that they are supposed to be friendly and talk to you but I don’t know it definitely seems different.

 

[mylolita]

1 minute ago, Kevin II said:

I kind of think so too but every time I think that I end up being wrong, well….except once.

I put everything down exactly as is, and yeah I know that they are supposed to be friendly and talk to you but I don’t know it definitely seems different.

 

Well I mean, my hairdresser doesn't personally text me or send me hearts and we don't exchange playlists! It's chatty and friendly and a little bit personal but that's about it. But I only go about 5 times a year! I mean, if the hairdresser was a man and he was doing this, I would suspect something more.

But you just have to take the plunge, it's the only way to know. So what if she says no? Just be a gentleman about it, there is absolutely no need for it to make anything awkward or for you to have to change salons or anything. If she says no, just say, I hope I haven't made anything awkward and we can still have our chats? No hard feelings?

And hopefully the air should be cleared if she is mature about it. 

Women are generally flattered, by the way, at just being asked. It will probably make her feel great even if she did say no. If she is kind and gracious, it will make her day and she will be complimented at the very least, and then you know where you stand, and you don't have to wonder, like Kwothe28 suggested!

Best,

x

[mylolita]

Just regarding the age gap thing, I realise it isn't the same for everyone, but there is nearly a 10 year age gap between me and my husband, and we first got together when I had just turned 18 and he was 28, and looked probably even worse because I was technically a teenager. We've been together 15 years and have 3 children too. 

I personally see nothing wrong with it. Women mature quicker than men in some regards, and when you get to "being in your 30s" and "being in your 40s" it's all the same to me. It just says, "Established adult, not too old, not too young!" 

x

[Andrina]

You won't like my advice at all, but I'll give it anyway. It doesn't matter if separating, and then moving toward divorce was her idea or not, but she won't be mentally ready, even if she says otherwise, to date until a good year after the divorce is finalized.

People need to go through all those stages that entail the end of a relationship, and get to know themselves again as a solo individual, before they can successfully try to date again.

She's actually been crossing relationship boundaries by getting too friendly with you and divulging her marital troubles with someone who has a crush on her--yes, she knows. Perhaps it's the reason her marriage is ending, because she doesn't know how to be a decent partner. She's still legally married, and it's unethical and unwise to make moves on a married woman.

IMO, 17 years is a very big age gap. When you project to the future, in general you'll likely be doing everything 17 years ahead of her--retirement, aging issues, dying, etc.

Doesn't seem like an egregious gap at the ages you both are now. But big differences start coming into play in ones 50s and 60s. That's why on OLD, there are plenty of guys in their 20s and 30s willing to ask out women in their 40s, but how many of them are asking out women in their 50s and 60s?

I've seen cases where the older person doesn't have their SO to hang out with in retirement years because the younger partner has to work another 15 to 20 years. And as I tell people, I'm glad my husband is 3 years younger. If he were 18 to 20 or more years older, I'd have to be handling his elderly problems as well as I've had to do with my elderly parents. Having to help with elderly parents is already stressful and tiring, so I don't want to also prematurely do this for my husband. And if I were the much older woman, I know I'd be too self-conscious about my wrinkles when my partner has far fewer. Some people could care less, though. 

Just my two cents.

 

[Kevin II]

1 hour ago, boltnrun said:

You have two people who are fresh out of romantic involvements. In her case she's still married.

You described your ex as the love of your life just today on your other thread. So it seems you still have that emotional attachment.

And do you know if this cosmetologist is separated because SHE wanted to be or did her husband initiate the separation? Is she still living with him? 

Are you always attracted to women who are nearly two decades younger? If so, why is that? I'm not saying it's wrong but it is unusual.

I would suggest asking her to have coffee so you can get a gauge on where the both of you are at.

 

 

Yes she was the love of my life but she cheated on me, we broke up a year ago, and she passed away a few months ago, so I certainly hope I can love again and don’t plan on just ending it all there. But I am super sad that she has died and I will always love her because of what we shared together.

With the age thing, it’s a coincidence, I was interested in somebody who was 50 years old a while ago but, we are friends from way back and it just didn’t seem like it would be a good connection.

And yes, she separated from her husband, she had been wanting to leave for a while, she tried to “fix” him and finally left not too long ago.

In our state you have to be separated for an entire year before you can file for divorce so it’s very common here for people that are separated to move on during that time.

 

 

[Kevin II]

34 minutes ago, Kwothe28 said:

Hairdressers are always talkative with customers. It kinda goes with the job because its in their interest for you to feel good so you would come back. Same with bartenders or any other profession where they depend on you coming back to spend your money there. So I wouldnt read as much as you into situation. She is like that with probably a lot of people.

 

OK, yeah I never really thought of that. It’s true. It still seems different though. I don’t know. Terrified of rejection in general so I’m not sure what I’m gonna do

[Kevin II]

17 minutes ago, Andrina said:

You won't like my advice at all, but I'll give it anyway. It doesn't matter if separating, and then moving toward divorce was her idea or not, but she won't be mentally ready, even if she says otherwise, to date until a good year after the divorce is finalized.

People need to go through all those stages that entail the end of a relationship, and get to know themselves again as a solo individual, before they can successfully try to date again.

She's actually been crossing relationship boundaries by getting too friendly with you and divulging her marital troubles with someone who has a crush on her--yes, she knows. Perhaps it's the reason her marriage is ending, because she doesn't know how to be a decent partner. She's still legally married, and it's unethical and unwise to make moves on a married woman.

IMO, 17 years is a very big age gap. When you project to the future, in general you'll likely be doing everything 17 years ahead of her--retirement, aging issues, dying, etc.

Doesn't seem like an egregious gap at the ages you both are now. But big differences start coming into play in ones 50s and 60s. That's why on OLD, there are plenty of guys in their 20s and 30s willing to ask out women in their 40s, but how many of them are asking out women in their 50s and 60s?

I've seen cases where the older person doesn't have their SO to hang out with in retirement years because the younger partner has to work another 15 to 20 years. And as I tell people, I'm glad my husband is 3 years younger. If he were 18 to 20 or more years older, I'd have to be handling his elderly problems as well as I've had to do with my elderly parents. Having to help with elderly parents is already stressful and tiring, so I don't want to also prematurely do this for my husband. And if I were the much older woman, I know I'd be too self-conscious about my wrinkles when my partner has far fewer. Some people could care less, though. 

Just my two cents.

 

 

I appreciate your input, thank you very much. I don’t think I stated this in the original post but here in our state you have to be separated for an entire year to even file for divorce so it’s pretty common for people that are separated to date here.

And psychologically I am pretty sure, very sure, that she checked out of that relationship a long time ago. They got married at like 20 and 21 years old, something like that. It seems like she’s been over it for a while. That’s what I gathered from what she was telling me.

I’m not necessarily saying I’m looking for another wife anytime soon. You can still have an amazing relationship with someone even if it runs its course after a few years.

With my former fiancé, the age gap really scared us at first but we realized that we just connected on so many levels. I’m a little more childlike and energetic and like to have a lot of fun and she was more mellow and laid-back even though she was much younger, and her friend once told me that if she only heard us but didn’t see us, she would think that we were the same age. 

I definitely feel like that with this person and I don’t think she’s looking for anything long-term and I don’t know if I am either. I just wanna spend time with her and see what happens because I like her quite a lot.

I’m still not sure what I’m going to do. But I don’t wanna miss out on it either, it just feels different this time.

Thanks again.

 

 

[boltnrun]

If you asked her out on a date and she said no, would you feel awkward or embarrassed?

[Kevin II]

10 minutes ago, boltnrun said:

If you asked her out on a date and she said no, would you feel awkward or embarrassed?

 

Yes!!! Definitely 

I could probably play it off though in person, but inside yes I would be crushed like Charlie Brown getting rejected by the little red haired girl

[Batya33]

5 minutes ago, Kevin II said:

 

Yes!!! Definitely 

I could probably play it off though in person, but inside yes I would be crushed like Charlie Brown getting rejected by the little red haired girl

Love Charlie Brown and the little red haired girl!  I agree with everything Andrina wrote.  I am married and I adore my hair stylist -he is also my husband's stylist.  I'm pretty sure he is gay.  We get along so well and click and I am there for hours (but I only go once or twice a year -my husband much more often for shorter time periods -and they also like each other).  I always assume that he goes out of his way to be so awesome to both of us because of the professional relationship (and he's the owner).  And honestly I think he genuinely likes us as people.

Also if she is going through the major transition of filing for divorce (no matter how long she's checked out of the marriage) and you ask her for coffee you're putting her in a really awkward position because very often during this transition finances and the financial situation is so important so she'll be concerned if she says no you may take your business elsewhere and stop referring others to her business (if you do).  So I'd wait a year after the divorce is final at least.  I also agree with Andrina that the age gap exarcebates the other issues.

[waffle]

1 hour ago, Andrina said:

 . . . there are plenty of guys in their 20s and 30s willing to ask out women in their 40s, but how many of them are asking out women in their 50s and 60s?

You'd be amazed.

[boltnrun]

2 hours ago, Kevin II said:

 

Yes!!! Definitely 

I could probably play it off though in person, but inside yes I would be crushed like Charlie Brown getting rejected by the little red haired girl

Is this a gamble you're willing to make?

Maybe it'll all work out OK and she'll say yes. But you have to plan for either outcome.

[mylolita]

It's easy for me to sit back here and say, "Just ask her out!" But, we're not messing with the nuclear codes here! 

The more you go back and forth about it, and build it up, the worse it's going to feel, the bigger it's going to feel. The fact you are thinking about this so much indicates you actually probably really like her.

Hairdressers and stylists are chatty, it's part of the job - this is more I would say, or more than I have heard of!

Someone can be fresh out of a divorce and ready to date the next day, some others take 5 years or more. Some peoples financial situations are ducks in a row, other's will never be settled, or unsure for years to come. There is no magic marker in time when it is finally okay to ask a separated or divorced lady out, in my opinion.

If she is a decent person, even if she did say no, she will respect the fact you stuck your neck out and asked, she really will. I think if most women were honest, it impresses us and flatters us to be asked, especially in person. Kudos. She can't take away from you the fact you had to confidence to do it. 

In the UK, our special forces SAS have a motto. Part of it is: "Who dares, wins."

You like her now! Now is the time! Life is too short! Cease the moment! 

x

[DarkCh0c0]

10 hours ago, Kevin II said:

She was married and now she is separated, even though mentally, I think she’s been separated for a while and has wanted to get out.

Separated or divorced?

Until she is fully divorced, I advise you keep your distance. Yes, this includes the 1 year wait to legally finalize the divorce.

Imagine if she changes her mind. Say, her ex pulls some romantic stunt and she goes back to him while dating you. That won't be fun.

However, if you insist on asking her out, I recommend you take things slow.

If she declines your invitation, I recommend you respond as lolita advised:

10 hours ago, mylolita said:

if she says no, just say, half jokingly, you've broke my heart, but you do a good cut, so I'll let you off 😉

Keep it lightheaded as you'll be coming back as a customer and you don't want it to be too awkward.

[mylolita]

9 hours ago, Kevin II said:

I kind of think so too but every time I think that I end up being wrong, well….except once.

I put everything down exactly as is, and yeah I know that they are supposed to be friendly and talk to you but I don’t know it definitely seems different.

 

I think so as well. If she is just toying with you and spending free time to somehow keep you as a customer, that is not good behaviour actually, and would look bad on her in my opinion, because she is crossing a private line just to keep customers. My gut instinct is she isn't doing that. 

If someone is giving you their time, especially outside of work, it normally means something. 

x

[DarkCh0c0]

9 hours ago, Andrina said:

IMO, 17 years is a very big age gap. When you project to the future, in general you'll likely be doing everything 17 years ahead of her--retirement, aging issues, dying, etc

I wholeheartedly agree. It's a huge gap. Almost 2 decades. They are in very different life stages in practice and they'll be like that for a long time.

8 hours ago, waffle said:

You'd be amazed

🧐 Can you elaborate?

[mylolita]

1 minute ago, DarkCh0c0 said:

Separated or divorced?

Until she is fully divorced, I advise you keep your distance. Yes, this includes the 1 year wait to legally finalize the divorce.

Imagine if she changes her mind. Say, her ex pulls some romantic stunt and she goes back to him while dating you. That won't be fun.

However, if you insist on asking her out, I recommend you take things slow.

If she declines your invitation, I recommend you respond as lolita advised:

Keep it lightheaded as you'll be coming back as a customer and you don't want it to be too awkward.

Thanks babe! Water off a ducks back, even if you are crushed. You can turn it over and analysis it when you get home! 

I really just say go for it. I mean, when is ever the perfect or right time for any kind of romantic love? There isn't any. Someone is always in the middle of study, career, already have children, medical issues, family issues, age issues, personal issues, mental issues. Lord, the list goes on. Finding someone you click with, who lifts you, gives you butterflies, is precious and rare and in my lil' ol' romantic opinion, should be chased. There is nothing worse than doing nothing, and then dealing with regrets. Regrets are worse than "she rejected me it hurt" because the "never know, could have been" aspect is often more mentally torturous.

x

[DarkCh0c0]

8 minutes ago, mylolita said:

really just say go for it. I mean, when is ever the perfect or right time for any kind of romantic love? There isn't any.

I agree to disagree on this one.

Wrong timing means wrong match. I say this from experience and friend' anecdotes. And, this isn't about a case of being busy with studies, an operation, ect. This is a case of someone not being single on paper. Legally, she is married. So he would be pursuing a married woman. Add to that, she might be working through break up baggage.

However, I did mention that if he insists on asking her out, to go slow or respond as you advised. I know life is life and people are different. There isn't always a straight right or wrong answer.

[mylolita]

8 minutes ago, DarkCh0c0 said:

I agree to disagree on this one.

Wrong timing means wrong match. I say this from experience and friend' anecdotes. And, this isn't about a case of being busy with studies, an operation, ect. This is a case of someone not being single on paper. Legally, she is married. So he would be pursuing a married woman. Add to that, she might be working through break up baggage.

However, I did mention that if he insists on asking her out, to go slow or respond as you advised. I know life is life and people are different. There isn't always a straight right or wrong answer.

Totally agree.

If my husband died, or I was divorced, I think deep down I wouldn't want to date seriously for years and years to come, and definitely never re-marry. Flings and casual things though, I don't know, maybe? Not sure. 

I suppose it depends.

I guess my other way of looking at this is, OP could wait a year, which is a very long time in some respects, just to find some other guy swooped and and whisked her off her feet the two months before the year was up, so to speak. When people are ready, they are ready, paper or no paper. She is fully separated I take it, so the rest is technical and financial and legal. Feelings don't normally care about stuff like that - well, mine anyway - HA! Feelings also don't care about age gaps. I think people fall for who they fall for. As long she the person isn't underage, I don't see a problem with two adults having a relationship, no matter what the age.

We can all accept the pros and cons to gaps. I accept with my husband being 9 years my senior, y'know, health issues might happen before me. But who's to say? All I know is, he's the love of my life and whatever happened, if he died tomorrow, we've had 15 years of bliss together and 3 beautiful children, and gap or no gap, nothing can change that for me.

I was told by my parents, don't go for him, especially as he was my first boyfriend. Everyone told me he's too old, or just after a younger girl. But we were, and are, genuinely in love. Our honeymoon phase never ended.  So my view on gaps, if it's just a genuine thing, and not an age difference that's chased for the age difference (as in, the guy will only strictly want an age gap) - if it's something organic that just so happens, what can you do? The age is just a sideline fact. Your heart is your heart. Cold hard life facts can come into play but, in my opinion, we can't base all our feelings and inner dreams and desires on logic. Or maybe you can, and it's just me - LOL!

x

[Wiseman2]

12 hours ago, Kevin II said:

 She said “thanks I really appreciate you and I really enjoy working with you.”

Sorry to say, but she has your contact info and hasn't done anything other than what typical hairdressers do chitchatting with clients. 

It seems like she knows you're hitting on her and therefore emphasized "working with you".

She doesn't want to be rude or lose a client, but she's trying to sidestep your advances diplomatically. 

Additionally, she's a captive audience and hears people's woes all day long. Unfortunately she already has TMI about your breakup.